Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins by quinidine-derived chiral amines

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	Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins by quinidine-derived chiral amines
	Shi M(施敏) ; Xu YM(徐永梅) ; Shi YL(时永灵)
刊名	Chem.-Eur. J.
	2005
卷号	11 期号:6 页码:1794-1802
其他题名	奎宁丁衍生的手性胺类化合物催化的不对称杂Baylis–Hillman Reaction
通讯作者	施敏
英文摘要	The chiral nitrogen Lewis base, tricyclic cinchona alkaloid derivative TQO, is an effective promoter in the catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines Ar-CH=NR' 1 (R' = Ts, Ms, Ns, SES) with various activated olefins such as methyl vinyl ketone (MVK), ethyl vinyl ketone (EVK), acrolein, methyl acrylate, phenyl acrylate, or alpha-naphthyl acrylate to give the corresponding adducts in moderate to good yields with good to high ee (up to 99%) at -30 degrees C or 45 degrees C in various solvents, including DMF/MeCN (1:1, v/v). The first such reaction of 1 with the simplest Michael acceptor MVK and methyl acrylate has been achieved with excellent enantioselectivity. The adducts derived from MVK and EVK had the opposite absolute configuration to those from acrolein, methyl acrylate, phenyl acrylate, and alpha-naphthyl acrylate. A plausible mechanism has been proposed on the basis of previous reports and the authors' investigations. An effective bifunctional chiral nitrogen Lewis base-Bronsted acid system has been revealed in this type of aza-Baylis-Hillman reaction.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1002/chem.200400872
语种	英语
WOS记录号	WOS:000227662900011
公开日期	2013-01-09
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/10002]
专题	上海有机化学研究所_金属有机化学国家重点实验室
推荐引用方式 GB/T 7714	Shi M,Xu YM,Shi YL. Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins by quinidine-derived chiral amines[J]. Chem.-Eur. J.,2005,11(6):1794-1802.
APA	Shi M,Xu YM,&Shi YL.(2005).Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins by quinidine-derived chiral amines.Chem.-Eur. J.,11(6),1794-1802.
MLA	Shi M,et al."Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins by quinidine-derived chiral amines".Chem.-Eur. J. 11.6(2005):1794-1802.